hydrogenchloride in 1,4-dioxane; water T=80°C; 1 h; further conditions: DMSO (BF3-Et2O), 95 deg C; Pd(PPh3)4, (CH2PPh2)2, toluene, 110 deg C; Yields of byproduct given;

1: HCl / dioxane; H2O / 1 h / 80 °C / further conditions: DMSO (BF3-Et2O), 95 deg C; Pd(PPh3)4, (CH2PPh2)2, toluene, 110 deg C 2: 1.) 4-NO2-C6H6-SO2-N3, 1,4-diazabicyclo<2.2.2>octan, 2.) tBuOCl, HCOOH, ascorbinic acid / 1.) DMF, 0 deg C, 2.) H2O, r.t., 1 h View Scheme

1: HCl / dioxane; H2O / 1 h / 80 °C / further conditions: DMSO (BF3-Et2O), 95 deg C; Pd(PPh3)4, (CH2PPh2)2, toluene, 110 deg C 2: 80 percent / NaNO2, NaOH, HCl / H2O / 7 h / 0 °C / further conditions: NaOCl, CH3COOH, r.t., 6 h View Scheme